Tips for Tackling Tough Conversations with Students

By Barbara Gruener

Tips for Tackling Tough Conversations with StudentsIt’s that time of year again—springtime, when students in your school family seem to know each other so well that they’re squabbling worse than siblings do, which means it might be time to don that helmet and those pads and tackle a tough conversation or two. How do you gently carefront your students while effectively confronting their issues, challenges, and struggles? What must you keep in mind as you courageously step out to positively shape those undesired behaviors so things go more smoothly as you run the race toward the finish line?

Consider trying these ten tips to help facilitate your next courageous convo:

  1. Pick your battles. Before initiating that tough conversation, make sure that the issue is one you really need to confront. Ask yourself: Is this conversation really important right now? What might happen if I put it off?
  2. Arm yourself with the facts. Resist the temptation to go headfirst into the conversation based on feelings, perceptions, hearsay, or secondhand information. Gather all the facts before the conversation and stick with them as you confront the issue. This will help you do your best to stay on target and to keep emotions from clouding the concerns.
  3. Play the tape to the end. When you’re about to tackle a tough conversation, consider Stephen Covey’s wisdom to begin with the end in mind. Play out in your head how the conversation might go, from start to finish. Better yet, write it down. What might the potential outcomes be? How will you know when you’ve achieved your goal?
  4. Request students’ presence. Extend an invitation to the student(s) involved to kindly carve out some time to meet and talk. Consider giving students a choice about when they can talk; a little lead time might be a nice gift so they can properly prepare for what’s coming their way. Make sure that they understand the urgency of your invitation so they aren’t tempted to miss this meeting.
  5. Be honestly bold. I’ll admit, this one can be really difficult. In fact, I’d rather play the Detective Colombo card, look puzzled, and beat around the bush. And sometimes that has been known to work. But in my three decades working as a caregiver, I’ve found that an honest, forthright approach works best for those courageous carefrontations. Cut to the chase, but make sure your boldness is assertive, not aggressive. Backing someone into a corner will put that person on the defensive and will not likely net the positive results you want or need.
  6. Ask poignant questions. Try open-ended, nonjudgmental prompts like: Help me understand this or, Tell me more. Then listen to really hear and embrace students’ answers. This can empower students and help them unlock errant thoughts to strengthen the desired outcomes—both theirs and yours.
  7. 10 Tips for Tackling Tough ConversationsListen with your whole body. Face students, lean in, look into their eyes, and nod to show your engagement so everyone involved in the conversation is fully invested in listening to understand. Body language and tone speak volumes too, so be sure to listen to what students are not saying—so you can hear and know what might be behind their behaviors.
  8. Practice empathy. Ask everyone involved to share their stories, then mirror back what you’ve heard them say and how you imagine they feel. As an alternative to this, ask students to share how another person might be feeling or what has been happening from the other person’s perspective first. Once empathy is elevated, the compassion and kindness that typically follow can serve to soften a volatile situation and facilitate negotiation.
  9. Talk with, not at. Always a great communication practice for healthy relationships, this is especially critical during conflict to make sure there’s give and take—that it’s a conversation rather than a sermon or a speech. A huge part of this is listening to understand rather than to respond. Remember that the goal of these tough conversations is to create a win-win rather than a win-lose.
  10. Focus on solutions. It can be tempting to go over and over the problem, to ruminate on what happened rather than seeking a solution. You might even want to punish and shame students. Don’t go there. Instead, invite students to brainstorm all solutions, even far-out or not-very-feasible ones. Ask them what they would like to see happen: If you had a magic wand, what would you change to help us move forward? Put all possible solutions on the table, then work together to come to a mutually agreeable end. Encourage students to own the problem, fix it, and move on. Then facilitate their ideas for restoration. Help them find a way they can not only apologize and say they’re sorry, but do sorry—put things back to where they were or set the wheels in motion toward a new normal.

When we decide to talk it out, we’re not only showing our students that we trust and value them enough to work with them through tough times, but we’re also modeling habits and skills that will serve students well as they follow suit and choose the peace path toward conflict resolution.

Barbara GruenerCurrently in her 34th year as an educator, Barbara Gruener, a school counselor and character coach at Bales Intermediate School in Friendswood, Texas, has had the pleasure of working with kids from every grade level. Author of the blog The Corner on Character and the book What’s Under Your Cape? SUPERHEROES of the Character Kind, Barbara enjoys positively influencing change through her inspirational keynotes and interactive workshops. When she’s not working, you can bet Barbara is knitting, baking, writing, reading, walking, gardening, napping, or spending time with her husband and their three children.


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